HRID2220373

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

HCID24822808

(3-(Cyclohexyloxy)-4-(methoxycarbonyl)phenyl)boronic acid

C14H19BO5

结构：CC(C)(C)OC(=O)N(CCc1ccc(Br)cc1)C[C@H](OC1CCCCO1)c1ccccc1

HCID86598946

未命名化合物

PRODUCTS

生成物

结构：COC(=O)c1ccc(-c2ccc(CCN(C[C@H](OC3CCCCO3)c3ccccc3)C(=O)OC(C)(C)C)cc2)cc1OC1CCCCC1

HCID69102956

未命名化合物

收率 83.1%

AUXILIARIES

试剂、催化剂与溶剂

结构：c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1

催化剂HCID178418397

未命名化合物

溶剂HCID962

Water

H2O

溶剂HCID8071

未命名化合物

溶剂HCID8857

Ethyl acetate

C4H8O2

CONDITIONS

反应条件

温度: 75 °C

PROCEDURE

实验过程

To a solution of tert-butyl [2-(4-bromophenyl)ethyl]-[(2R)-2-phenyl-2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-carbamate (620 mg) in 1,2-dimethoxyethane (7 ml) were added [3-(cyclohexyloxy)-4-(methoxycarbonyl)phenyl]boronic acid (410 mg), tetrakis(triphenylphosphine)palladium (99 mg) and aqueous solution of sodium carbonate (2M, 1.35 ml), and the mixture was stirred at 75° C. for 5 hours under nitrogen. The mixture was diluted with ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=9/1) to give methyl 4′-[2-[(tert-butoxycarbonyl)[(2R)-2-phenyl-2-(tetrahydro-2H-pyran-2-yloxy)ethyl]amino]ethyl]-3-(cyclohexyloxy)-4-biphenylcarboxylate (672 mg).

WORKUP

后处理

customThe organic layer was separated
washwashed with brine
dry with materialdried over magnesium sulfate
customevaporated under reduced pressure
customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=9/1)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-71ea15d203c44d3b8e15117b07289541
来源数据集: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07417060B2

反应 SMILES

Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH2:18][C@@H:19]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:4][CH:3]=1.[CH:33]1([O:39][C:40]2[CH:41]=[C:42](B(O)O)[CH:43]=[CH:44][C:45]=2[C:46]([O:48][CH3:49])=[O:47])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:13]([O:12][C:11]([N:10]([CH2:18][C@@H:19]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1)[CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:42]2[CH:43]=[CH:44][C:45]([C:46]([O:48][CH3:49])=[O:47])=[C:40]([O:39][CH:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)[CH:41]=2)=[CH:3][CH:4]=1)=[O:17])([CH3:16])([CH3:15])[CH3:14]